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WO2019077039A1 - Concentré liquide pour la conservation - Google Patents

Concentré liquide pour la conservation Download PDF

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Publication number
WO2019077039A1
WO2019077039A1 PCT/EP2018/078543 EP2018078543W WO2019077039A1 WO 2019077039 A1 WO2019077039 A1 WO 2019077039A1 EP 2018078543 W EP2018078543 W EP 2018078543W WO 2019077039 A1 WO2019077039 A1 WO 2019077039A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
products
composition according
benzoic acid
anyone
Prior art date
Application number
PCT/EP2018/078543
Other languages
English (en)
Inventor
Stephan SAKULOWSKI
Original Assignee
Schülke & Mayr GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schülke & Mayr GmbH filed Critical Schülke & Mayr GmbH
Priority to JP2020519991A priority Critical patent/JP7337785B2/ja
Priority to BR112020007102-1A priority patent/BR112020007102B1/pt
Priority to KR1020207012513A priority patent/KR20200067165A/ko
Priority to US16/755,653 priority patent/US11638426B2/en
Publication of WO2019077039A1 publication Critical patent/WO2019077039A1/fr
Priority to US18/189,298 priority patent/US12302899B2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18

Definitions

  • the invention relates to an antimicrobial liquid concentrate and the use of said liquid concentrate for preservation, particularly of cosmetic products, i.e. wet wipes.
  • Preservatives based on carboxylic acids such as benzoic acid, sorbic acid, de- hydroacetic acid, undecylenic acid, or salts thereof are known. Although such acids and salts are toxicologically safe, they are not sufficiently effective when used alone. The cosmetic industry therefore continues to seek improved preservatives based on organic acids.
  • DE 4026756 A1 discloses a preservative comprising from 5 wt.% to 60 weight% (wt.%) of an organic acid selected from benzoic acid, 4-hydroxy benzoic acid, salicylic acid, formic acid, acetic acid, propionic acid, sorbic acid, undecylenic acid, and/or dehy- droacetic acid and salts thereof; from 10 wt.% to 95 wt.% of aromatic alcohols, and from 0.1 wt.% to 20 wt.% of poly(hexamethylenebiguanide) salts; optionally 0.1 wt.% to 20 wt.% of substituted glycerol ethers and/or solvents such as water, glycols such as pro- pyleneglycol, dipropyleneglycol, and triethyleneglycol, or glycol ethers such as butyl di- glycol, in order to improve low-temperature stability.
  • an organic acid selected from benzoic acid,
  • euxyl ® K 702 Another known product is euxyl ® K 702, produced by Schijlke & Mayr GmbH (Norderstedt, Federal Republic of Germany), which comprises benzoic acid, poly(hexa- methylene biguanide) hydrochloride, dehydroacetic acid, and phenoxyethanol.
  • cationic surfactants such as poly(hexamethylene biguanide) salts
  • anionic surfactant-based products such as shampoos is problematic, because this can result in interactions causing the formation of precipitates or deactivation.
  • DE 10122380 A1 discloses an alcohol-free liquid concentrate, for example for the preservation of cosmetics, which comprises a carboxylic acid component (A), a stabilizer component (B), and solvents (C).
  • the carboxylic acid component (A) comprises at least one salt of benzoic acid, propionic acid, salicylic acid, sorbic acid, 4-hydroxy benzoic acid, dehydroacetic acid, or 10-undecylenic acid, and optionally one or a plurality of the above-mentioned free acids.
  • Illustrative concentrates described in said document in addition contain up to approximately 45 wt.% of a mixture of sodium benzoate with potassium sorbate, formaldehyde or a formaldehyde depot compound (such as dimethylol dimethyl hydantoin).
  • a formaldehyde depot compound such as dimethylol dimethyl hydantoin.
  • WO 2012/151441 A1 describes antimicrobial formulations which comprises a fatty acid and at least one natural product or product of natural origin, such as 1 ,3-pro- panediol or an alcohol-containing solvent, or an organic acid or salt thereof such as potassium sorbate or benzoic acid.
  • WO 2012/151441 A1 discloses an anhy- drous mixture comprising approximately 80 wt.% 1 ,3-propanediol, 10 wt.% (ethylhexyl) glycerol, and 10 wt.% potassium sorbate.
  • the preservatives according to this document are used in skin care products such as shampoos, lotions, conditioners and soaps.
  • compositions containing e.g. potassium sorbate and sodium benzoate cannot be formulated as clear solutions, if the content of sorbate and benzoate is too high and/or the content of 1 ,3-propanediol is two. Although 1 ,3-propanediol alone is readily soluble in water, it is not possible to prepare a clear solution from 45 wt.% of water, 15 wt.% of potassium sorbate, and 30 wt.% of sodium benzoate with 10 wt.% of 1 ,3-propanediol. Moreover, the formulations according to WO2012/151441 A1 act as thickeners, which is a drawback in use for the preservation of wet wipes.
  • PCT/EP2017/069722 filed on 03 rd August 2017 discloses an aqueous antimicrobial liquid concentrate, which comprises from 5 wt.% to 20 wt.% of one or a plurality of diols selected from alkanediols having from six to twenty carbon atoms, and monoalkyl glycerol ethers having from four to eighteen carbon atoms, from 20 wt.% to 60 wt.% of one or a plurality of salts of one or a plurality of organic acids selected from the group composed of sorbic acid, benzoic acid, anisic acid, salicylic acid, 4-hydroxy benzoic acid, cinnamic acid, succinic acid, and levulinic acid, and optionally one or a plurality of the above-mentioned free acids, and from 30 wt.% to 70 wt.% of water, wherein the content of aromatic alcohol is a maximum of 5 wt.% relative to the weight of the liquid concentrate
  • compositions of organic acids and aromatic alcohols are already known in the form of a concentrate.
  • Aromatic alcohols are in public discussion because of the possible potential of sensitisation. Therefore, there is a need of microbiologically active composi- tions which do not comprise any aromatic alcohols, additional combination partners must fulfil the criteria of cosmetic ingredients. They must be storage stable, soluble, processa- ble and result in a clear composition in the final concentrate.
  • Water-free cosmetic products require water-free preservation to avoid an additional amount of water which offers condition for microbiological growth. Therefore, the composition must have antimicrobial activity and good compliance properties, combined with use in low-water of water-free systems.
  • the present invention aims to provide preservatives as concentrates, that can easily be formulated into clear solutions, even in an aqueous dilution.
  • the preservative should have little or no effect on the properties of the final product and therefore need not necessarily contain surfactants, emulsifiers, solvents or aromatic alcohols.
  • the invention therefore relates to a composition, which com- prises:
  • the composition as hereinbefore defined is free from aromatic alcohol.
  • aromatic alcohols mainly mean alcohols, such as phenoxyethanol, phenoxypropanol, phenethyl alcohol, phenyl propanol and benzylic al- cohol, and which are commonly used in the formulation of cosmetics products, household products or technical products.
  • composition as hereinbefore defined is free from water.
  • the invention relates to a composi- tion as hereinbefore defined, wherein the weight ratio 1 ,2-octanediol/benzoic acid is equal to 1.
  • the invention relates to a composition as hereinbefore defined, wherein the weight ratio 1 ,2-octanediol/propylene glycol is greater or equal to 0.2 and less or equal to 0.5; and/or to a composition as hereinbefore defined, wherein the weight ratio benzoic acid/propylene glycol is greater or equal to 0.2 and less or equal to 0.5.
  • the invention relates to a composition as hereinbefore defined, which consists in, for 100% of its weight:
  • composition as hereinbefore defined is characterized by a weight ratio 1 ,2-octane- diol/benzoic acid equal to 1 ; and said composition more specifically consists in, for 100% of its weight:
  • the invention also relates to the use of a composition as hereinbefore defined, for the preservation of cosmetics products, household products or technical products and/or as a disinfectant.
  • the invention relates to the use of a composition as hereinbefore defined for the preservation of wet wipes.
  • the invention also relates to a method to preserve cosmetics products, household products or technical products, characterized in that an efficient amount of a com- position as hereinbefore defined, is added in the mixture of the constituents of said cosmetics products, household products or technical products, during the preparation of said cosmetics products, household products or technical products, such as a wet wipe.
  • an efficient amount approximatively means a weight proportion of approximately from 0.05 wt.% to 3% wt.% of said cosmetics prod- ucts, household products or technical products.
  • TSA tryptone-soy agar
  • 25 cm 3 of the end solutions are each inoculated with 0.1 cm 3 of microorganism suspensions (initial microorganism count: approximatively 10 9 cfu/ml).
  • the solutions are streaked out onto TSA after 3, 6, 24 and 48 hours.
  • the cultures are incubated for 48 hours at 37°C.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Toxicology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition qui comprend : a) de 15 % en poids à 25 % en poids de 1,2-octanédiol, b) de 15 % en poids à 25 % en poids d'acide benzoïque,c) de 50 % en poids à 70 % en poids de propylène glycol, la teneur en alcool aromatique étant inférieure ou égale à 5 % en poids par rapport au poids du concentré liquide ; l'utilisation d'une composition, pour la conservation de produits cosmétiques, de produits ménagers ou de produits techniques.
PCT/EP2018/078543 2017-10-18 2018-10-18 Concentré liquide pour la conservation WO2019077039A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2020519991A JP7337785B2 (ja) 2017-10-18 2018-10-18 防腐用液体濃縮物
BR112020007102-1A BR112020007102B1 (pt) 2017-10-18 2018-10-18 Concentrado líquido para preservação
KR1020207012513A KR20200067165A (ko) 2017-10-18 2018-10-18 보존을 위한 액체 농축액
US16/755,653 US11638426B2 (en) 2017-10-18 2018-10-18 Liquid concentrate for preservation
US18/189,298 US12302899B2 (en) 2017-10-18 2023-03-24 Liquid concentrate for preservation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP17197082.5 2017-10-18
EP17197082.5A EP3473097A1 (fr) 2017-10-18 2017-10-18 Concentré liquide pour la conservation

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US16/755,653 A-371-Of-International US11638426B2 (en) 2017-10-18 2018-10-18 Liquid concentrate for preservation
US18/189,298 Continuation US12302899B2 (en) 2017-10-18 2023-03-24 Liquid concentrate for preservation

Publications (1)

Publication Number Publication Date
WO2019077039A1 true WO2019077039A1 (fr) 2019-04-25

Family

ID=60138302

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2018/078543 WO2019077039A1 (fr) 2017-10-18 2018-10-18 Concentré liquide pour la conservation

Country Status (7)

Country Link
US (1) US11638426B2 (fr)
EP (1) EP3473097A1 (fr)
JP (1) JP7337785B2 (fr)
KR (1) KR20200067165A (fr)
CN (1) CN109673637B (fr)
BR (1) BR112020007102B1 (fr)
WO (1) WO2019077039A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200345611A1 (en) * 2019-04-30 2020-11-05 Evonik Operations Gmbh Composition comprising at least one ceramide, at least one sphingoid base and triethyl citrate
WO2022006507A1 (fr) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Compositions végétales antimicrobiennes stables

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DE19922538A1 (de) 1999-05-10 2000-11-16 Schuelke & Mayr Gmbh Flüssig-Konzentrat zur Konservierung von Kosmetika
DE10122380A1 (de) 2001-05-09 2002-11-28 Schuelke & Mayr Gmbh Alkoholfreies Flüssig-Konzentrat zur Konservierung von kosmetischen, Haushalts- und technischen Produkten
WO2012151441A1 (fr) 2011-05-04 2012-11-08 Lincoln Manufacturing Inc. Compositions antimicrobiennes naturelles
EP2873321A1 (fr) * 2013-11-15 2015-05-20 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Concentré liquide pour l'équipement antimicrobien de produits devant être appliqués topiquement

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DE19922538A1 (de) 1999-05-10 2000-11-16 Schuelke & Mayr Gmbh Flüssig-Konzentrat zur Konservierung von Kosmetika
DE10122380A1 (de) 2001-05-09 2002-11-28 Schuelke & Mayr Gmbh Alkoholfreies Flüssig-Konzentrat zur Konservierung von kosmetischen, Haushalts- und technischen Produkten
WO2012151441A1 (fr) 2011-05-04 2012-11-08 Lincoln Manufacturing Inc. Compositions antimicrobiennes naturelles
EP2873321A1 (fr) * 2013-11-15 2015-05-20 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Concentré liquide pour l'équipement antimicrobien de produits devant être appliqués topiquement

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200345611A1 (en) * 2019-04-30 2020-11-05 Evonik Operations Gmbh Composition comprising at least one ceramide, at least one sphingoid base and triethyl citrate
WO2022006507A1 (fr) * 2020-07-02 2022-01-06 The Trustees Of Columbia University In The City Of New York Compositions végétales antimicrobiennes stables

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Publication number Publication date
KR20200067165A (ko) 2020-06-11
CN109673637B (zh) 2022-10-14
BR112020007102B1 (pt) 2023-11-28
BR112020007102A2 (pt) 2020-09-24
JP7337785B2 (ja) 2023-09-04
EP3473097A1 (fr) 2019-04-24
CN109673637A (zh) 2019-04-26
JP2021500319A (ja) 2021-01-07
US20230225318A1 (en) 2023-07-20
US11638426B2 (en) 2023-05-02
US20210368791A1 (en) 2021-12-02

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